Flavor and fragrance compositions containing thiopyran-carbaldehyde
a technology of thiopyrancarbaldehyde and composition, which is applied in the field of flavor and fragrance materials, can solve the problems of not being able to isolate and/or confirm any proposed molecules, not being able to achieve the effect of improving, enhancing or modifying a flavor or a fragrance composition
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example i
[0031]
Preparation of 2,6-Dipropyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde (Formula I)
[0032]Sodium methoxide (CH3ONa) (16.2 g, 0.3 mol) was dissolved in methanol (MeOH) (100 mL). 3-(Acetylthio)-hexanal (25 g, 0.1 mol) was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for additional 2 hours. Ice water (200 mL) was then added and the reaction mixture was acidified with hydrogen chloride (HCl) (10%) to pH 2. The resulting mixture was extracted with ethyl acetate (EtOAc) (200 mL). The organic layer was washed successively with brine, sodium bicarbonate solution (NaHCO3) (10%) and brine, dried and concentrated to provide a crude product. The crude product was distilled and further purified with a silica gel column (ethyl acetate / hexanes) to afford 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde (12 g).
[0033]1H NMR (CDCl3, 400 MHz): 9.32 (s, 1H), 6.79 (dd, 1H, J=5.3, 2.8 Hz), 3.51 (m, 1H), 2.92-3.05 (m, 1H), 2.61-2.75 (m, 1H), 2....
example ii
[0035]
Preparation of 2,6-Dimethyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde (Formula II)
[0036]2,6-Dimethyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde (4.8 g) was similarly prepared using S-(4-oxobutan-2-yl)-ethanethioate (100 g, 0.684 mol).
[0037]1H NMR (CDCl3, 500 MHz): 9.33 (s, 1H), 6.80 (dd, J=5.4, 2.5 Hz, 1H), 3.70 (q, J=6.9 Hz, 1H), 3.10-3.18 (m, 1H), 2.67-2.74 (m, 1H), 2.24-2.40 (m, 1H), 1.47 (d, J=6.9 Hz, 3H), 1.34 (d, J=6.6 Hz, 3H)
example iii
[0038]
Preparation of 5,6-Dihydro-2H-thiopyran-3-carbaldehyde (Formula III)
[0039]Bis(3,3-diethoxypropyl)sulfane (50 g, 0.17 mol), water (69.4 mL, 3.855 mol), p-toluenesulfonyl chloride (1.619 g, 8.49 mmol) and 1,4-dioxane (100 mL, 1.174 mol) were combined and stirred at 80° C. for about 2 hours. The reaction was cooled to room temperature. Water was added and the reaction mixture was extracted with diethyl ether ((C2H5)2O). The organic layer was washed successively with saturated sodium bicarbonate solution, water and brine, and then dried and concentrated to provide a crude product. The crude product was further purified with a silica gel column (ethyl acetate / hexanes, 1:20) to afford 5,6-dihydro-2H-thiopyran-3-carbaldehyde (3.2 g).
[0040]1H NMR (CDCl3, 400 MHz): 9.37 (s, 1H), 6.86-6.96 (m, 1H), 3.29-3.36 (m, 2H), 2.79 (t, J-5.6 Hz, 2H), 2.63-2.72 (m, 2H)
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